Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Previous problemNext problem

2:44 minutes

Problem 49a

Textbook Question

What product is obtained from ring-opening metathesis polymerization of each of the following compounds? (Hint: In each case, the product is an unsaturated hydrocarbon with a high molecular weight.)
a.

Verified step by step guidance

Step 1: Identify the compound provided in the image. The structure is a bicyclic compound containing a strained cyclobutene ring fused to a cyclohexene ring. The double bond in the cyclohexene ring is the reactive site for ring-opening metathesis polymerization (ROMP).

Step 2: Understand the mechanism of ring-opening metathesis polymerization (ROMP). ROMP involves the cleavage of a strained cyclic alkene, followed by polymerization through a metathesis reaction. The driving force is the release of ring strain, leading to the formation of a linear polymer.

Step 3: Predict the product of ROMP. The polymerization will result in a high molecular weight unsaturated hydrocarbon. The repeating unit in the polymer corresponds to the structure of the monomer after the ring has opened. The double bond in the monomer will remain in the polymer chain, contributing to unsaturation.

Step 4: Analyze the structure after ring opening. The cyclobutene ring opens to form a linear chain, while the cyclohexene ring contributes to the repeating unit. The polymer will consist of alternating double bonds along the backbone, maintaining the unsaturation characteristic.

Step 5: Conclude the product. The product is a linear unsaturated hydrocarbon polymer with repeating units derived from the monomer. The polymer backbone will contain alternating double bonds, resulting in a conjugated system with high molecular weight.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Ring-Opening Metathesis Polymerization (ROMP)

ROMP is a type of polymerization that involves the opening of a cyclic compound to form a polymer. This process typically utilizes transition metal catalysts to facilitate the reaction, allowing for the formation of unsaturated polymers. The reaction is characterized by the exchange of alkene groups, leading to the creation of long-chain hydrocarbons with high molecular weights.

Unsaturated Hydrocarbons

Unsaturated hydrocarbons are organic compounds that contain at least one double or triple bond between carbon atoms. These compounds are significant in organic chemistry as they can undergo various reactions, including polymerization. The presence of double bonds in the product of ROMP contributes to the reactivity and properties of the resulting polymer, making it useful in various applications.

Molecular Weight in Polymers

Molecular weight refers to the mass of a molecule, and in the context of polymers, it indicates the size of the polymer chains formed during polymerization. High molecular weight polymers typically exhibit enhanced mechanical properties and stability. Understanding the relationship between the starting monomer and the resulting polymer's molecular weight is crucial for predicting the material's behavior and applications.

Watch next

Master Intro to Predict the Product with a bite sized video explanation from Johnny

Start learning